Alexander Payne and His Road Trips (MINOR SPOILERS)
The filmmaker, Alexander Payne, made three films about road trips, each of them very individual, yet all of them related to each other in certain ways:
About Schmidt: Newly retired and suddenly widowed, Schmidt(Jack Nicholson) drives from Nebraska to Colorado to attend his daughter's wedding.
Sideways: Another wedding angle: middle-aged minor celebrity horndog Jack( Thomas Hayden Church) takes his long-time "opposites attract" buddy Miles(Paul Giamatti on a Southern California road trip to the Santa Barbara County wine region. Jack's Goal -- get laid before he has to get married, and maybe get his pal laid, too.
Nebraska: A different angle entirely: a stoic, edge-of-dementia old man (Bruce Dern) thinks the standard sweepstakes letter ("You may have won 1,000,000!) is a real guarantee of a million, and compels one of his sons to drive him from his home in Montana to Nebraska to pick up money he'll never really get.
Schmidt and Nebraska have the strongest link. The old Nicholson's old wife who dies early on in Schmidt(Jane Squibb) is the same actress who plays the very elderly wife of the very elderly Dern in Nebraska. And Squibb survives in Nebraska. Interesting: Payne first offered the elderly lead in Nebraska to Nicholson, who turned it down and recommended his friend Dern for the part(in the 70's, Dern got a few roles that Nicholson turned down.) So Nebraska could have been a "sequel" of sorts to Schmidt, with Nicholson and Squibb reunited as husband and wife and playing an even older, and more toxic, couple. (Seeing Squibb 11 years after Schmidt, in Nebaska, shows us how age REALLY catches up with you in your final decades.
As it turns out, Nicholson feels right for Schmidt, and Dern feels right for Woody Grant. Schimdt is an insurance executive and a more successful man than the old man in Nebraska, whose background is as a garage owner, a mechanic...and too much of a drunk to have succeeded at either. Nicholson as we find him has most of his mental faculties intact; Dern does not(though rational thought and sentences keep emerging from him, there is no particular "follow up"; he speaks and then fades back away.)'
Both "Schmidt" and "Nebraska" are ultimately about family bonds, and finds them tight and strangling at the same time. Schmidt has but one child, a daughter who has grown up to be an angry neurotic and believes her father neglected her(he probably did, but she's pretty annoying on her own, and marrying into a family of total weirdos to her father's horror.) A retirement to be based on travelling around with his wife is destroyed when the wife dies right at the start of the film. . We sense that Schmidt will HAVE to reconcile more with his daughter, and probably fit into her new, weird family , as best he can. He has nowhere else to go.
Whereas Squibb in Schmidt merely bossed him around(made him sit to urinate, told him not to "dilly dally" when going shopping) Squibb in Nebraska puts Dern down constantly and makes like she wants him "in a home." As the movie rolls along, we see the premium that Squibb put on her youthful sexuality versus "other girls" to win men...and she turns her anger away FROM Dern to protect him against the family vultures who want some of the money he doesn't have.
Initially, only one of Dern's two sons(Will Forte) has the empathy to drive the old man on a trip to disappointment(there is no one million dollars waiting) but the more antagonistic family members(Squibb as the mother. Bob Odenkirk being Saul Goodman as the other son) join up, follow along and -- demonstrate the meaning of family even if the patriarch is almost mentally gone.
And so "About Schmidt" and "Nebraska" are about a trip of discovery, and suprising family ties, and the terrors of "the end of life," be it with retirement at 66 or dementia in one's 70's. And even with all these "old people," memories of sex -- or continued desire FOR sex -- are part of the journey.
Which brings us to Sideways. Because the two main characters are unmarried middle-aged men...sex is still very much on their minds: the horndog's all the time(he has a beautiful woman ready to marry him and you can figure he'll barely be faithful to her), the more nerdly wine connoisseur in terms of a marriage lost to drink and divorce and a buried belief that maybe another woman will find him attractive, after all. The men in Sideways are younger than Schmidt or Woody and their goals are different(neither is of retirement age yet), but their road trip mirrors those of Schmidt and Woody because, though "not much happens" in terms of high drama...a LOT happens in terms of self-discovery.
And though there are no adult children to the men in Sideways, one of them is the adult child OF a living mother. The visit to her solo existence in a Ventura apartment happens early in Sideways and brings that story its own "family connection."